I heart Chicago.
It's official, Chicago is on my list of cities that, were I to suddenly become God (unlikely), I would scoop up and move to Texas. That may sound ridiculous to you, but if it does you're probably not from Texas. Just saying. Other cities on this list are Buenos Aires, San Francisco, Denver, London, and Charlotte.
Chicago makes the list because it's a beautiful city and it's strikingly well planned compared to the midwestern city I live in. It's the little things. The freeway has express lanes with exits only at the major streets and local lanes with exits at every street. There is a well developed and utilized public transit system. Someone is paying traffic cops to keep an eye and direct traffic at almost every major intersection. Everything has an accurate and easy to understand sign. There are parks throughout downtown and things happen there. By "things" I mean events other than muggings or soirees with hookers.
I can't imagine ever being bored in Chicago. Is that possible? There are so many museums and restaurants and parks and bars and events that you would have to be terminally dull to not come up with something to do. Then there's the history: The Mob, riots, prohibition, baseball, the fire, the railroad, and Oprah. Yup, Chicago is definitely my new "city crush," and right at Valentine's Day (oh yeah, there's the Valentine's Day Massacre as well).
My one complaint is that it is cold in a way I just can't handle, and not for a brief period every year. It is cold with a capital C for a few months every year. I mean, I'd be thinking marriage with Chicago were it not for the cold...and the wind. Like Katt Williams says, you have to buy your coat from there for there. This is part of the reason that, were I to suddenly become God (still unlikely), I would move Chicago to Texas. You can't change cities though, you have to love them for what they are.
Ah Chicago, we could have been perfect for one another.